A kind of synthetic method of aryl methyl selenide compound

A synthesis method and methyl selenide technology are applied in the field of synthesis of aryl methyl selenide compounds, can solve the problems of poor functional group tolerance, complicated operation of aryl methyl selenide compounds and the like, and achieve simple operation and simple post-processing. , the effect of simple post-processing operation

Inactive Publication Date: 2019-09-06
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] The first technical problem to be solved by the present invention is the problem of complicated operation in the preparation process of aryl methyl selenide compound
[0019] The second technical problem to be solved by the present invention is the poor tolerance of functional groups in the preparation process of aryl methyl selenide compounds
[0020] The third technical problem to be solved by the present invention is the problem that the preparation process of aryl methyl selenide compound is suitable for large-scale industrial production

Method used

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  • A kind of synthetic method of aryl methyl selenide compound
  • A kind of synthetic method of aryl methyl selenide compound
  • A kind of synthetic method of aryl methyl selenide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Synthesis of 4-methoxy-2-nitrophenylmethyl selenide

[0067]

[0068] At room temperature, 2-nitro-4-methoxybenzoic acid (0.4mmol, 1equiv), Cu(OAc) 2 (0.04mmol), 1,10-phenanthroline (0.04mmol), potassium carbonate (1.2mmol, 3equiv) and 2mL toluene join in the reaction tube, fill with oxygen then, and replace three times, under oxygen reaction environment, Then dimethyl diselenide (0.8mmol, 2equiv) was added and stirred at a reaction temperature of 140°C for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then ethyl acetate was added to filter, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether=98: 2), and the product was Yellow liquid, yield 85%, product weight 84mg.

[0069] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0070] 1 H NMR (500MHz, CDCl 3 ): δ7.84(d, J=2.8Hz, 1H), 7.36(d, ...

Embodiment 2

[0077] Synthesis of 2-nitro-4-trifluoromethylphenylmethylselenide

[0078]

[0079] At room temperature, 2-nitro-4-trifluoromethylbenzoic acid (0.4mmol, 1equiv), Cu(OAc) 2 (0.04mmol), 1,10-phenanthroline (0.04mmol), potassium carbonate (1.2mmol, 3equiv) and 2mL toluene join in the reaction tube, fill with oxygen then, and replace three times, under oxygen reaction environment, Then dimethyl diselenide (0.8mmol, 2equiv) was added and stirred at a reaction temperature of 140°C for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then ethyl acetate was added to filter, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether=98: 2), and the product was Yellow liquid, yield 80%, product weight 91mg.

[0080] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0081] 1 H NMR (500MHz, CDCl 3 ): δ8.59(s, 1H), 7....

Embodiment 3

[0088] Synthesis of (2-methylselenylphenyl)phenyl ketone

[0089]

[0090] At room temperature, 2-benzoylbenzoic acid (0.4mmol, 1equiv), Cu(OAc) 2 (0.04mmol), 1,10-phenanthroline (0.04mmol), potassium carbonate (1.2mmol, 3equiv) and 2mL toluene join in the reaction tube, fill with oxygen then, and replace three times, under oxygen reaction environment, Then dimethyl diselenide (0.8mmol, 2equiv) was added and stirred at a reaction temperature of 140°C for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then ethyl acetate was added to filter, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether=98: 2), and the product was Yellow liquid, yield 49%, product weight 54mg.

[0091] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0092] 1 H NMR (500MHz, CDCl 3 ): δδ7.77-7.75(m, 2H), 7.59-7.52(m, 3H), 7.4...

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Abstract

The invention relates to a synthetic method of an aryl methyl selenide compound. In an organic solvent, under the oxygen condition, aryl carboxylic acid and dimethyldiselenide are used as reaction raw materials to obtain the aryl methyl selenide compound through oxidative decarboxylation coupling reaction under the joint promoting effect of a copper catalyst, a ligand and alkaline. The aryl carboxylic acid and the copper catalyst adopted in the method are cheap and easy to obtain, a substance range is wide, the reaction condition is simple, the product yield and purity are high, a new synthetic route and method is developed for the aryl methyl selenide compound, and the aryl methyl selenide compound has good utilization potential and a research value.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of an aryl methyl selenide compound. Background technique [0002] Selenium-containing organic compounds widely exist in biological structures and functional molecules, such as animal offal, fish, seafood, mushrooms, eggs, garlic, and ginkgo. Selenium has anti-cancer, anti-oxidation, enhanced human immunity, Antagonize harmful heavy metals, regulate vitamin absorption, regulate protein synthesis in the human body, and enhance reproductive function. It is also an important component of peroxidase in muscles and seminal plasma. Scientists call it the "king of anti-cancer" of human trace elements ". [0003] So far, selenium has been widely used in the synthesis of medicine, polymer materials, and pesticides. For example, a number of drug molecules containing selenoether structures have been developed: Ebselen (Ebselen) was develope...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C391/02C07D333/62C07D307/82
Inventor 吴戈
Owner WENZHOU MEDICAL UNIV
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